4-Methylmorpholine → N,N-dimethyl-beta-alanine, [2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazol-1-yl]-methyl ester

HRID 1493216노트

반응식

HRID 1493216 반응식
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH3:24][O:25][C:26]1[C:31]([CH3:32])=[CH:30][N:29]=[C:28]([CH2:33][S:34]([C:36]2[N:40]([CH2:41]O)[C:39]3[CH:43]=[CH:44][CH:45]=[CH:46][C:38]=3[N:37]=2)=[O:35])[C:27]=1[CH3:47].[OH-].[Na+]>C(Cl)Cl>[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][C:5]([O:7][CH2:41][N:40]1[C:39]2[CH:43]=[CH:44][CH:45]=[CH:46][C:38]=2[N:37]=[C:36]1[S:34]([CH2:33][C:28]1[C:27]([CH3:47])=[C:26]([O:25][CH3:24])[C:31]([CH3:32])=[CH:30][N:29]=1)=[O:35])=[O:6]

참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 62365Isobutyl chloroformateHCID 2398283-(Dimethylamino)propanoic acidHCID 15282209HCID 15282209, 화합물

생성물 1

HCID 56993588N,N-dimethyl-beta-alanine, [2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazol-1-yl]-methyl ester수율 32%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

반응 조건

온도
-10 °C

실험 절차

N,N-dimethyl-β-alanine (0.76 g 0.005 mol) and N-methyl morpholine (0.99 g 0.01 mol) was added to CH2Cl2 (15 ml). The solution was cooled to -10° C. and isobutylchloroformate, (0.68 g 0.005 mol) dissolved in CH2Cl2 (15 ml), was added under inert atmosphere. The solution was stirred for about 20 min at -10° C. [2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]-sulfinyl]-1H-benzimidazol-1-yl]methanol dissolved in CH2Cl2 (15 ml) was added dropwise to the mixed anhydride at -10° C. The solution was stirred 2 h at -10°, and the temperature was thereafter raised to room temperature. NaOH solution (25 ml 0.24) was added under stirring and the mixture was stirred for about 5 min. After separation the CH2Cl2 phase was dried over Na2SO4, filtered and the solution was evaporated off, giving the desired compound (yield 0.7 g 32%). The identity of the title compound was confirmed with NMR.

후처리

  1. additionwas added under inert atmosphere
  2. temperaturethe temperature was thereafter raised to room temperature
  3. stirringunder stirring
  4. stirringthe mixture was stirred for about 5 min
  5. customAfter separation the CH2Cl2 phase
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered
  8. customthe solution was evaporated off

출처 및 근거

ORD 기록
ord-387b34c927814828aae85fd828baf022
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05021433

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